WO1999006013A2

WO1999006013A2 - Agent and method for permanent shaping of hair and method for the production of n-alkylmercaptoacetamides

Info

Publication number: WO1999006013A2
Application number: PCT/EP1998/004361
Authority: WO
Inventors: Beate Dannecker; Günther LANG; Wolfgang Hanefeld; Heiko Walther
Original assignee: Wella Aktiengesellschaft
Priority date: 1997-07-31
Filing date: 1998-07-14
Publication date: 1999-02-11
Also published as: JP3964938B2; WO1999006013A3; JP2001504138A; EP0969791A2; ES2212338T3; DE59810341D1; US6264932B1; EP0969791B1

Abstract

The object of the invention is an agent for permanent shaping of hair, characterised in that it contains an N-alkylmercaptoacetamide of formula (I) wherein R represents a straight-chain alkyl radical with 3-6 carbon atoms or a straight-chain hydroxy alkyl radical with 3-6 carbon atoms or the salts thereof as an active keratin-reducing substance. The invention also relates to a method for producing N-alkylmercapto- acetamides of formula (I). The agent enables mild and homogenous shaping of hair and has a 2-9.5 pH range that is gentle towards the skin and hair without causing allergic and sensitizing reactions.

Description

DESCRIPTION

Means and methods for permanent hair shaping and methods for the production of N-alkylmercaptoacetamides

The present invention relates to an agent for permanent hair styling based on straight-chain NC ₃ - to C ₆ -alkyl- or NC ₃ - to C ₆ -hydroxyalkyl-substituted mercaptoacetamides as keratin-reducing active ingredient and a method for permanent hair shaping using this agent.

As is well known, the classic technique for performing a permanent one is based

Hair shaping in two treatment steps: In the first step, the cstin disulfide bridges of hair keratin are opened by the action of an agent that contains a reducing agent (shaping agent). Then the hair is brought into the desired shape. In a second step, cystine disulfide bonds are made using a fixative, i.e. of an agent containing an oxidizing agent, closed again.

As a classic permanent wave reducing agent, as the pioneering work in German patents 948 186 and 972 424 show, thioglycolic acid, e.g. used as the ammonium or monoethanolamine salt. Other common reducing agents are inorganic sulfites, 2-mercapto-propionic acid (thiolactic acid), 3-mercapto-propionic acid, cysteine and derivatives of these compounds as well as certain mercaptocarboxylic acid esters.

Alkaline preparations based on the mercaptocarboxylic acids show hair damage despite sufficient action, which manifests itself, for example, in increased hair breakage. In many cases, these agents also have an undesirable impact on the scalp. Finally, the unpleasant smell of the reducing agents used requires intensive perfuming of the products. By using 2-mercapto-propionic acid one is able to solve some of the problems mentioned. However, the thiolactic acid shows a weaker transformation compared to the commonly used thioglycolic acid. For a gentle, permanent shaping of damaged, in particular bleached or dyed hair, weakly acidic to neutral shaping agents are preferably used. From a technical point of view, thioglycolic acid esters have proven to be the most suitable reducing agents for this purpose over the past 35 years.

A considerable disadvantage of acidic hair styling agents based on thioglycolic acid esters is their poor eye and skin tolerance and the sensitizing effect of thioglycolic acid esters, so that the use of these hair shaping agents is largely dispensed with today. Instead of the mercaptocarboxylic acid esters, mercaptocarboxamides such as thioglycolic acid amide or alkyl- or hydroxyalkyl-substituted amides were also used. Such compounds are known from the patents DE-C-1 144 440 and EP-A-0 455457. Like the mercaptocarboxylic acid esters, these substances have a high conversion potential at low pH values, but are even more critical than the mercaptocarboxylic acid esters in terms of their toxicological properties.

The invention is therefore based on the object of providing an agent and a process for permanent hair shaping which are suitable both in the acidic and in the weakly alkaline range (pH = 2 to 9.5), especially in the pH range from 4. 0 to 8.5, enables a gentle and even shaping, has no or only a slight sensitization potential and also has a greater shaping potential than 2-mercaptopropionic acid (thiolactic acid).

It has now surprisingly been found that the disadvantages mentioned can be avoided by using certain N-alkylmercaptoacetamides and that these have a greater conversion potential than thiolactic acid.

The present invention therefore relates to an agent for permanent shaping of the hair, which is characterized in that it is an N-alkylmercaptoacetamide of the formula as a keratin-reducing active ingredient

(l),

wherein R represents a straight-chain alkyl radical having 3 to 6 carbon atoms or a straight-chain hydroxyalkyl radical having 3 to 6 carbon atoms, or its salt.

R is preferably a straight-chain alkyl radical with 3 carbon atoms or a straight-chain hydroxyalkyl radical with 3 carbon atoms.

The straight-chain hydroxyalkyl radical should preferably have one or two hydroxyl groups.

Preferred N-alkylmercaptoacetamides of the formula (I) are N-propyl-2-mercaptoacetamide, N- (2'-hydroxypropyl) -2-mercaptoacetamide and N- (3'-hydroxypropyl) -2-mercaptoacetamide.

Particularly suitable salts are the hydrogen salts with the acids hydrochloric acid, sulfuric acid, acetic acid or citric acid.

The N-alkylmercaptoacetamide of the formula (I) is preferably contained in the agent as the sole keratin-reducing active ingredient. However, it can also in combination with other keratin-reducing agents - such as thioglycolic acid, thiolactic acid, 2-hydroxy-3-mercapto-propionic acid, cysteamine and cysteamine derivatives such as alkyl or acylcystamine or cysteine and cysteine derivatives, e.g. B. cysteine (2-hydroxyethyl) ester or L-cysteine glycerol ester or sulfites - are used.

The N-alkylmercaptoacetamide of the formula (I) is used in the ready-to-use agent for permanent hair shaping in an amount of 3 to 28 percent by weight, preferably 5 to 21 percent by weight. The ready-to-use hair styling agents preferably have a pH of 2.0 to 9.5, particularly preferably 4.0 to 8.5. Alkalizing agents or agents for adjusting the pH are, in particular, ammonia or sodium hydroxide solution, but also water-soluble, physiologically tolerable salts of organic and inorganic bases, such as, for example, ammonium hydrogen carbonate. In particular, hydrochloric acid, acetic acid or citric acid can be used to set an acidic pH.

The shaping agent can be packaged in one or two or three components, the agent being in the form of an aqueous solution or an emulsion or in thickened form on an aqueous basis, in particular as a cream, gel, foam or paste.

Of course, the shaping agent can contain all additives which are customary and known for such agents, for example thickeners, such as, for example, bentonite, fatty acids, starch, polyacrylic acid and their derivatives, cellulose derivatives, alginates, petroleum jelly, paraffin oils; Wetting agents or emulsifiers from the classes of anionic, cationic, amphoteric or nonionic surface-active substances, for example fatty alcohol sulfates, fatty alcohol ether sulfates, alkyl sulfonates, alkylbenzenesulfates, quaternary ammonium salts, alkyl betaines, oxethylated alkylphenols, fatty acid alkanoamides or oxyethylated fatty acid esters; opacifiers, such as polyethylene glycol esters; Alcohols, such as ethanol, propanol, isopropanol, polyols such as e.g. B. 1, 2- or 1, 3-propanediol, 1, 2-, 1.3- or 1, 4-butanediol, 1, 2-pentanediol and glycerol; Sugar such as B. D-glucose; Solubilizers, stabilizers, buffer substances, perfume oils, dyes and hair conditioning and hair care ingredients, such as cationic polymers, lanolin derivatives, cholesterol, pantothenic acid and betaine, contain.

The constituents mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in a total concentration of 0.2 to 30 percent by weight, the alcohols in a total amount of 0.1 to 20 percent by weight, the opacifiers, perfume oils and dyes in an amount of 0.01 to 1 percent by weight, the buffer substances in a total amount of 0.1 to 10 percent by weight, sugar, solubilizers, stabilizers, and hair conditioning and hair care ingredients in an amount of 0.1 to 5 percent by weight while the thickeners and solvents Mediators in a total amount of 0.5 to 20 percent by weight can be included in this agent.

So-called swelling and penetration substances, such as dipropylene glycol monomethyl ether, 2-pyrrolidone or imidazolidin-2-one, can also be added to this agent to increase the activity, in an amount of 1 to 30 percent by weight and to avoid over-frizzing the hair, dithio compounds, for example dithiodiglycolic acid, dithiolactic acid Disulfides of the compounds mentioned or their salts are added.

By varying the pH value, an agent can be made available that is universally suitable for any hair structure, possibly with the additional application of heat. The agent effects an elastic, permanent and even shaping from the hairline to the tip of the hair without causing allergic or sensitizing reactions.

The present invention further relates to a method for permanent hair shaping, in which the hair is treated with a shaping agent before and / or after it is brought into the desired shape, rinsed with water, then treated oxidatively, rinsed with water, optionally laid in a water wave and then drying, which is characterized in that the agents according to the invention described above are used as the shaping agent.

In a preferred embodiment of the method according to the invention, the hair is first washed with a shampoo and then rinsed with water. The towel-dried hair is then divided into individual strands and wound on curlers with a diameter of 5 to 30 millimeters, preferably 5 to 15 millimeters. The hair is then treated with an amount, preferably 60 to 120 grams, of the shaping agent according to the invention described, which is sufficient for hair shaping.

After an exposure time sufficient for permanent shaping of the hair, which, depending on the nature of the hair, the pH value and the shaping effectiveness of the shaping agent and depending on the application temperature, 5 to 30 minutes (10 to 30 minutes without heat; 5 to 20 minutes with Exposure to heat), the hair is rinsed with water and then oxidatively post-treated ("fixed"). The post-treatment agent is used, depending on the fullness of the hair, preferably in an amount of 80 to 100 grams.

Any post-treatment agent suitable for such a treatment can be used for the oxidative after-treatment in the wound or unwound state. Examples of oxidizing agents which can be used in such post-treatment agents are potassium and sodium bromate, sodium perborate, urea peroxide and hydrogen peroxide. The concentration of the oxidizing agent varies depending on the application time (usually 5 to 15 minutes) and the application temperature. The oxidizing agent is normally present in the ready-to-use aqueous aftertreatment agent in a concentration of 0.5 to 10 percent by weight. The agent for the oxidative aftertreatment can of course contain other substances, such as wetting agents, care substances such as cationic polymers, weak acids, buffer substances or peroxide stabilizers, and in the form of an aqueous solution, an emulsion and in thickened form on an aqueous basis, in particular as Cream, gel or paste. These customary additives can be contained in the aftertreatment agent in particular in an amount of 0.1 to 10% by weight. The winders are then removed. If necessary, the unwound hair can now be treated oxidatively again. Then the hair is with

Rinsed water, if necessary put to the water wave and finally dried.

Quite surprisingly, the preferred N-alkylmercaptoacetamides N-propyl-2-mercaptoacetamide, N- (2'-hydroxypropyl) -2-mercaptoacetamide and N- (3'-hydroxypropyl) -2-mercaptoacetamide have significantly lower sensitization rates than that N-alkylmercaptoacetamides, N-methyl-mercaptoacetamide and N-hydroxyethyl-mercaptoacetamide known from the prior art according to DE-C-1 144 440 or EP-A-0 455 457 as the closest permanent wave active ingredients.

The N-alkylmercaptoacetamide of the formula (I) is prepared by reacting the corresponding amine at a temperature not above 30 degrees Celsius with methylthioglycolate under a protective gas atmosphere, extraction in a suitable solvent and subsequent short-path distillation.

The following examples are intended to explain the subject matter of the invention in more detail, without, however, restricting the subject matter to these examples.

MANUFACTURING EXAMPLES

Example 1 Preparation of N-Propyl-2-mercaptoacetamide

118 g (2 mol) of n-propylamine are placed in a 500 ml three-necked flask. 106.24 g of methylthioglycolate are slowly added dropwise in such a way that the temperature does not exceed 30 ° C. The mixture is flushed with argon and stirred at room temperature for 2 days.

The mixture is acidified with 36 percent hydrochloric acid while cooling with ice (pH 2-4) and extracted exhaustively with ethyl acetate. The solvent is distilled off in vacuo on a circulation evaporator, the residue is brought to pH 7.0 by adding sodium hydroxide solution and extracted again with ethyl acetate. The combined fractions are dried over sodium sulfate and concentrated. The residue present is distilled to a pure product using a short path distillation apparatus at a maximum of 0.01 torr. The yield is 115 g (86%).

Analytics:

a) ¹ H-NMR (CDCI ₃ ): δ (ppm) = 6.79 (bulbous, -NH)

3.20 (t, 2H, + NH-CH ₂ )

3.20 (s, 2H, HS-CH ₂ -CO)

1.85 (bulbous, 1 H, HS)

1.52 (m, 2H, NH-CH-CH ₂ )

0.90 (t, 3H, CH ₂ -CH ₃ )

δ (ppm) = 169.18 (-C = O)

41.83 (NH-CH)

28.36 (HS-CH ₂ )

22.72 (NH-CH-CH ₂ -CH ₃ ) 11, 37 (CH ₂ -CH ₃ )

c) MS (70 e V, El, RT) m / z (%) = (M ⁺ ) = 133 (47.68)

100 (29.1), 86 (24.58), 58 (8.6), 47 (25.67),

43 (100)

d) Thiol titration: 95.78%

e) Elemental analysis: C ₅ HnNOS (MG: 133.21)

Calc .: C 45.08, H 8.32, N 10.51, S 24.07 Found: C 44.72, H 8.12, N 10.18, S 23.71

f) IR (NaCI plates):

3293s (NH)

3084-2876S (CH ₂ )

2552w (SH)

1652s (N-monosubstituted amide)

1559s (N-monosubstituted amide)

g) HPLC: The HPLC gave a result of 98.07 area percent for the

Connection.

(Column: C 18 5U, 250 mm x 4.6 mm; flow agent acetonitrile: buffer [4 g KH ₂ P04 + 0.8 g octanesulfonic acid Na salt + 2 ml H ₃ P0 ₄ ] = 25:75; flow rate 0. 5 ml / min; wavelength 200 nm;)

h) pKs: 8.451 (H ₂ 0)

i) UV-max: 209.8 nm (acetonitrile: buffer = 25:75)

j) Boiling point: 76 ° C / 0.01 Torr Example 2 Preparation of N- (2 ^{'hydroxypropyl)} -2-mercaptoacetamide

150.22 g (2 mol) of 1-amino-2-propanol are placed in a 500 ml three-necked flask. 106.24 g (1 mol) of methyl mercaptoacetate are slowly added dropwise in such a way that the temperature does not exceed 30 ° C. The mixture is flushed with argon and stirred at room temperature for 2 days.

The mixture is acidified with 36 percent hydrochloric acid while cooling with ice (pH 2-4) and extracted exhaustively with ethyl acetate. The solvent is distilled off in vacuo on a circulation evaporator, the residue is brought to pH 7.0 by adding sodium hydroxide solution and extracted again with ethyl acetate. The combined fractions are dried over sodium sulfate and concentrated. The residue present is distilled using a short path distillation apparatus at a maximum of 0.01 Torr to the pure product. The yield is 95 g (64%).

Analytics:

a) ¹ H-NMR (CDCI ₃ ):

δ _H (ppm) = 6.70 (bulbous, -NH)

3.93 (m, 1H, CH)

3.44 and 3.14 (m, each 1 H, NH-CH ₂ )

3.26 (s, 2H, HS-CÜ-CO)

2.07 (t, 1 H, HS)

1, 21 (d, 3H, CH ₃ )

b) ¹³ C-NMR (CDCI ₃ ):

δ _c (ppm) = 170.71 (-C = 0)

67.00 (NH-CH ₂ -CH)

47.38 (NH-CH _? )

28.24 (HS-CH ₂ )

20.87 (Cü,) c) MS (70 e V, El, RT) m / z (%) = (M ⁺ ) = 149 (8.39)

131 (47.08), 105 (100), 84 (27.49), 72 (72.76), 58 (57.75), 56 (32.11), 47 (59.94)

d) Thiol titration: 97.88%

e) Elemental analysis: C ₆ H ₁₃ NOS (MW: 149.21)

Calc .: C 40.25, H 7.43, N 9.39, S 21, 49 Found: C 40.11, H 7.42, N 9.12, S 21, 53

f) IR (KBr):

3314s (OH)

3090-2927S (CH ₂ )

2549w (SH)

1657s (N-monosubstituted amide)

1554s (N-monosubstituted amide)

g) HPLC: The HPLC gave a result of 98.88 area percent for the

Connection.

(Column: C 18 5U, 250 mm x 4.6 mm; superplasticizer acetonitrile:

Buffer [4 g KH ₂ PO4 + 0.8 g octanesulfonic acid Na salt + 2 ml

H ₃ P0 ₄ ] = 25:75; Flow rate 0.5 ml / min; Wavelength 200 nm;)

h) pKs: 7.865 (H ₂ 0)

i) UV-max: 218.0 nm (acetonitrile: buffer = 25: 75)

j) Boiling point: 108 ° C / 0.01 Torr

Example 3 Preparation of N- (3'-hydroxypropyl) -2-mercaptoacetamide

150.22 g (2 mol) of 3-amino-1-propanol are placed in a 500 ml three-necked flask. 106.24 g (1 mol) of methyl mercaptoacetate slowly become such added dropwise that the temperature does not exceed 30 ° C. The mixture is flushed with argon and stirred at room temperature for 2 days.

The mixture is acidified with 36 percent hydrochloric acid while cooling with ice (pH 2-4) and extracted exhaustively with ethyl acetate. The solvent is distilled off in vacuo on a circulation evaporator, the residue is brought to pH 7.0 by adding sodium hydroxide solution and extracted again with ethyl acetate. The combined fractions are dried over sodium sulfate and concentrated. The residue present is distilled using a short path distillation apparatus at a maximum of 0.01 Torr to the pure product. The yield is 63 g (42%).

Analytics:

a) ¹ H-NMR (CDCI ₃ ):

δ _H (ppm) = 7.062 (bulbous, -NH)

3.64 (m, 2H, CH ₂ -OH)

3.42 (m, 2H, CH ₂ .CH ₂ -CH ₂ -OH)

3.22 (d, 2H, HS-CÜ-CO)

2.04 (t, 1H, CH ₂ -OH)

1.72 (t, 1 H, HS)

1.69 (m, 2H, CH ₂ -CH _? -CH ₂ -OH)

b) ¹³ C-NMR (CDCI ₃ ):

δ _c (ppm) = 170.59 (-C = O)

59.86 (NH-CH ₂ )

37.06 (CH2-OH)

31.99 (CH ₂ -CH ₂ -CH ₂ -OH)

28.53 (HS-CH _? )

c) MS (70 e V, El, RT) m / z (%) = (M ⁺ ) = ^■ 149 (36.1: 3)

131 (36.58), 116 (31.62), 105 (23.15), 102 (100), 84

(72.8), 76 (24.49), 56 (66.29) 12

d) Thiol titration: 94.063%

e) Elemental analysis: C ₅ HnNOS (MW: 149.21)

Calc .: C 40.25, H 7.43, N 9.39, S 21, 49 Found: C 40.21, H 6.99, N 9.05, S 21, 53

f) IR (NaCI):

3299s (NH)

3086-2918s (CH ₂ )

2546w (SH)

1651s (N-monosubstituted amide)

1551s (N-monosubstituted amide)

g) HPLC: The HPLC gave a result of 93.19 area percent for the

Connection.

(Column: C 18 5U, 250 mm x 4.6 mm; superplasticizer acetonitrile:

Buffer [4 g KH ₂ PO4 + 0.8 g octanesulfonic acid Na salt + 2 ml

H ₃ P0 ₄ ] = 25:75; Flow rate 0.5 ml / min; Wavelength 200 nm;)

h) pKs: 8.406 (H ₂ 0)

i) UV-max: 223.2 nm (acetonitrile: buffer = 25:75)

j) Boiling point: 115 ° C / 0.01 Torr

Example 4 Comparison of corrugation effectiveness

The well activity of the compound was determined using glycerol monothioglycolate as a reference substance with the aid of Wellösungeπ at pH = 7, 8 and 9. For this purpose, 16.5 centimeters long, pre-bleached and damaged hair strands (consisting of approx. 100 hairs) from Central European hair were wound up on standardized spiral winders (inside diameter: 3 millimeters) and after conditioning in the climatic room (temperature: 20 ° C; humidity: 65%) with a 87 mmol / 100g containing, adjusted to the respective pH Solution of the reducing agent treated. The amount of corrugated liquid applied was calculated using the ratio 1: 1.2 (1 g of hair: 1, 2 ml of corrugated liquid). 20 minutes were chosen as the exposure time; the exposure temperature was 50 degrees Celsius. The hair was then fixed with a peroxide-containing fixation, dried and, after unwinding, hung in water for four hours (water bath temperature: 40 ° C.).

The wave stability is calculated according to the following formula: lo - lt

Well stability in% x 100

10 lo - m

l ₀ = total length of the unformed, stretched strand (16.5 centimeters)

it length of the unwound, unhinged strand after 240 minutes h length of the reshaped, wound strand

15 (with a winding inner diameter of 3 millimeters this is 35 millimeters)

Table 1

0 As a standard, highlights were adjusted to pH 9 accordingly Glycerin monothioglycolate solution treated. The standardized wave stabilities (WSN) given above in Table 1 refer to this standard solution (pH = 9), the wave stability of which was set to 100 percent.

Table 1 shows that the waving efficacies of the mercaptoacetamides according to the invention are higher at pH 7, 8 and 9 than with thiolactic acid.

EXAMPLES OF PERMANENT MOLD

Example 5 Permanent shaping agent for colored hair

10.8 g of N-propyl-2-mercaptoacetamide

0.4 g ammonia (25% aqueous solution) for pH adjustment

2.0 g ammonium hydrogen carbonate

5.0 g isopropanol

2.5 g 1,2 propylene glycol

2.5 g of 1,2-pentanediol

1.0 g of isooctylphenol, oxethylated with 10 mol of ethylene oxide

1.0 g poly (dimethyldiallylammonium chloride)

0.3 g of perfume oil

0.1 g vinyl pyrrolidone / styrene copolymer

(Antara® 430 from GAF Corp .; New York / USA)

74.4 g water

100.0 g The pH of this product is 7.3.

Hair damaged by color treatments is washed with a shampoo, terry toweling and wound on rollers with a diameter of 8 millimeters. Then the hair styling agent described above is evenly distributed on the wound hair. The hair is then covered with a plastic hood and under a drying hood for 10 minutes at a temperature of Heated to 45 degrees Celsius. The cover is then removed, the hair rinsed with water and oxidatively aftertreated with 100 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried.

The result of this treatment is an even, elastic and permanent deformation of the hair.

Example 6 Perm for normal hair

14.5 g of N-propyl-2-mercaptoacetamide

8.9 g ammonia (25% aqueous solution)

4.0 g of ammonium bicarbonate

1.0 g 1,3-butanediol

5.0 g 1,2 propylene glycol

2.0 g dipropylene glycol monoethyl ether

4.0 g urea

2.5 g hydrogenated castor oil, oxethylated with 40 moles of ethylene oxide

2.5 g lauric alcohol, ethoxylated with 4 mol ethylene oxide (CTFA: Laureth-4)

0.5 g perfume oil

0.1 g vinyl pyrrolidone / styrene copolymer (Antara® 430 from GAF Corp .; New York / USA)

55.0 g water

100.0 g

The pH of this product is 8.4.

Normal, undamaged hair is washed, terry with a towel and wound on curlers with a diameter of 6 millimeters. Then The hair is moistened evenly with the hair styling agent described above. After an exposure time of 15 minutes, the hair is rinsed thoroughly with water and then oxidatively aftertreated with 80 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried. The hair treated in this way has an even and lively frizzy.

Example 7 Permanent shaping agent for normal hair

7.7 g of N-propyl-2-mercaptoacetamide

8.7 g of N- (2'-hydroxypropyl) -2-mercaptoacetamide

8.9 g ammonia (25% aqueous solution) for pH adjustment

5.0 g ammonium hydrogen carbonate

1.0 g of 1,2-propanediol

2.0 g D-glucose

2.4 g ammonia

1.5 g of isooctylphenol, oxethylated with 10 mol of ethylene oxide

0.5 g poly (dimethyldiallylammonium chloride)

0.5 g perfume oil

61.7 g of water

100.0 g The pH of this agent is 8.3.

Normal, undamaged hair is washed, terry with a towel and wound on curlers with a diameter of 6 millimeters. The hair is then moistened evenly with the hair styling agent described above. After an exposure time of 15 - 25 minutes, the hair is rinsed thoroughly with water and then with 80 grams of a 3- percent aqueous hydrogen peroxide solution oxidatively aftertreated. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried. The hair treated in this way has an even and lively frizzy.

Example 8 Two-component permanent shaping agent for normal hair

Component A

4.5 g ammonium bicarbonate

0.4 g ammonia, 25% for pH adjustment

2.0 g diethylene glycol monoethyl ether

2.0 g of 1-methoxypropanol

1.5 g propylene glycol

0.5 g oleyl alcohol polyethylene glycol ether-5EO (CTFA: OLETH-5)

0.5 g quaternary ammonium salt of the terpolymer from acrylic acid / diallyldimethylammonium chloride / acrylamide (CTFA: POLYQUATERNIUM-39) Commercial product: Merqua Plus 3330

0.5 g perfume oil

88.1 g water

100.0 g

Component B

50.0 g of N- (2'-hydroxypropyl) -2-mercaptoacetamide, 94%

To use the two-component permanent waving agent, 60 g of component A are mixed with 14 g of component B to form a ready-to-use hair styling agent. Mixing creates a product with a pH of 6.5.

Normal, undamaged hair is washed, terry with a towel and wound on curlers with a diameter of 6 millimeters. Then The hair is moistened evenly with the ready-to-use hair styling agent described above. After an exposure time of 15-25 minutes, the hair is rinsed thoroughly with water and then oxidatively treated with 80 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried. The hair treated in this way has an even and lively frizzy hair and provides an excellently trained, stable permanent wave.

Example 9 Permanent shaping agent for normal hair

7.7 g of N-propyl-2-mercaptoacetamide

8.7 g of N- (3'-hydroxypropyl) -2-mercaptoacetamide

5.0 g isopropyl alcohol

1.0 g of 1,2-propanediol

0.5 g coconut oil alcohol, ethoxylated with 10 moles of ethylene oxide

0.5 g perfume oil

0.1 g vinyl pyrrolidone / styrene copolymer

(Antara® 430 from GAF Corp .; New York / USA)

76.5 g water, fully desalinated

100.0 g The pH of this agent is 4.5.

Normal, undamaged hair is washed, terry with a towel and wound on curlers with a diameter of 6 millimeters. The hair is then moistened evenly with the hair styling agent described above. After an exposure time of 15-25 minutes, the hair is rinsed thoroughly with water and then oxidatively treated with 80 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried. The hair treated in this way has a frizzle which is uniform over the entire length of the hair and which is comparable to the frizzy hair obtained by treatment with mildly alkaline permanent shaping agents. Example 10 Permanent shaping agent for colored hair

13.7 g N- (3'-hydroxypropyl) -2-mercaptoacetamide, 90%

4.4 g ammonia (25% aqueous solution) for pH adjustment 2.0 g ammonium hydrogen carbonate

2.0 g dipropylene glycol monoethyl ester

2.5 g of 1,2-propylene glycol

1.0 g poly (dimethyldiallylammonium chloride)

0.3 g of perfume oil

2.5 g phosphoric acid ester of decyl alcohol oxethylated with 4 mol ethylene oxide (CTFA: DECETH-4 PHOSPHATE)

71.6 g of water

100.0 g

The pH of this product is 7.3.

Hair damaged beforehand by color treatments is washed with a shampoo, terry toweling and wound on rollers with a diameter of 8 millimeters. Then the hair styling agent described above is evenly distributed on the wound hair. The hair is then covered with a plastic hood and heated for 10 minutes under a drying hood at a temperature of 45 degrees Celsius. The cover is then removed, the hair is rinsed with water and oxidatively aftertreated with 100 grams of a 3 percent aqueous hydrogen peroxide solution. After removing the curlers, the hair is rinsed again with water, placed in a water wave and then dried.

Claims

PATENT CLAIMS

1. Agent for permanent shaping of hair, characterized in that it is an N-alkylmercaptoacetamide of the formula as a keratin-reducing agent

(I).

2. Composition according to claim 1, characterized in that the N-alkylmercaptoacetamide of the formula (I) is selected from N-propyl-2-mercaptoacetamide, N- (2'-hydroxypropyl) -2-mercaptoacetamide and N- (3'- Hydroxypropyl) -2-mercaptoacetamide.

3. Composition according to one of claims 1 or 2, characterized in that the N-alkylmercaptoacetamide of formula (I) is contained in the ready-to-use agent in an amount of 3 to 28 percent by weight.

4. Agent according to one of claims 1 to 3, characterized in that the pH of the ready-to-use agent is 4 to 8.5.

5. Agent according to one of claims 1 to 4, characterized in that it is obtained before use by mixing two or three components.

6. A process for permanent shaping of hair, in which the hair is treated with a shaping agent before and / or after it is held in the desired shape, rinsed with water, oxidatively aftertreated, rinsed again with water, if necessary placed in a water wave and then drying, characterized in that an agent according to one of Claims 1 to 4 is used as the shaping agent.

7. The method according to claim 6, characterized in that the deforming agent is allowed to act for 5 to 30 minutes.

8. The method according to claim 6 or 7, characterized in that the shaping agent is allowed to act for 5 to 20 minutes using heat.

9. The method according to any one of claims 6 to 9, characterized in that the shaping agent is used in an amount of 60 to 120 grams.

10. A process for the preparation of an N-alkylmercaptoacetamide of the formula (I), characterized in that the corresponding amine is reacted with methylthioglycolate at a temperature not above 30 degrees Celsius, and the product is purified by a short path distillation.